Spider-Man has had a lot of cartoons over the years, and oh God almighty riding a unicycle while wearing a tutu do I mean a LOT.
Being Marvel's biggest cash cow, the wall-crawler has been on the small screen practically since inception, all the way back in the 60s and continuing until...well now, basically, with there always being at least one Spider-Man cartoon on the air per decade.
Everyone's got their favorites, but no matter which one you love, each has their fair share of dark moments. Spider-Man's one of the all-time sad sack superheroes, and as such, any good adaptation of the material is going to have some dire moments to make Spidey nice and sad.
From the 90s Spider-Man that was many millennials' first introduction to the character, to the tragically short-lived Spectacular Spider-Man, to the others that I will mention under protest because they're nowhere near as good, these are the darkest storylines, episodes, and scenes in all of animated Spider-Man.
10. Harry Osborn Is The Green Goblin - Spectacular Spider-Man
By now, we all know how the Green Goblin story plays out. First it's Norman Osborn, and then it's Harry who inherits the mantle after his dad dies in a fight with Spider-Man. So when the Green Goblin showed up in Greg Weisman's Spectacular Spider-Man, we were all prepared for that being where everything was going.
But the first rule of children's television is and has always been: never assume you're a step ahead of Greg Weisman.
Leading up to the big reveal, we see Harry grow more and more confident and socially popular through a strange green substance that he wolfs down like tic-tacs. This of course was the Goblin formula, and we see it all come together as Spidey unmasks the Green Goblin, convinced it's Norman, only to find Harry under the mask, to the shock and horror of both him and Harry's father.
Seeing that Harry is thoroughly messed up long before Norman becomes the Goblin, let alone dies, was a shocking moment for any kid watching, especially kids who had seen the then recent Raimi movies and knew how this was "supposed" to go.